2-Hexadecanol - ≥95% , CAS No.14852-31-4

CAS: 14852-31-4 Cat. No.: H346541 Fórmula: C₁₆H₃₄O Peso molecular: 242.44

GRAU & PUREZA ≥95%

Synonyms

CHEBI:185029 | Hexadecan-2-ol | AI3-35278 | SCHEMBL259176 | NSC 87605 | 4-CHLORO-5-CYANOQUINOLINE | Methyl tetradecyl carbinol | NSC87605 | NSC-87605 | J-008480 | 2-Hexadecanol, 99% | DTXSID80871235 | EINECS 238-917-5 | AKOS009157550 | 2-Hexadecanol | FT-

Storage

Room temperature

Shipped In

Normal

Especificações

Sinónimos

CHEBI:185029 | Hexadecan-2-ol | AI3-35278 | SCHEMBL259176 | NSC 87605 | 4-CHLORO-5-CYANOQUINOLINE | Methyl tetradecyl carbinol | NSC87605 | NSC-87605 | J-008480 | 2-Hexadecanol, 99% | DTXSID80871235 | EINECS 238-917-5 | AKOS009157550 | 2-Hexadecanol | FT-

Especificações e pureza

≥95%

Condições de armazenamento de armazenamento

Room temperature

Enviado em

Normal

Pureza

≥95%

Nomes e identificadores

Pubchem Sid

488186344

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/488186344

Sorrisos canónicos

CCCCCCCCCCCCCCC(C)O

IUPAC Name

hexadecan-2-ol

InChIKey

FVDRFBGMOWJEOR-UHFFFAOYSA-N

INCHI

1S/C16H34O/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16(2)17/h16-17H,3-15H2,1-2H3

SMILES isoméricas

CCCCCCCCCCCCCCC(C)O

Peso molecular

242.44

Reaxy-Rn

1748421

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1748421&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Classe Fatty Acyls
      • Subclass Fatty alcohols

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Classe: Fatty Acyls
• Subclass: Fatty alcohols
• Intermediate Tree Nodes: Not available
• Direct Parent: Long-chain fatty alcohols
• Alternative Parents: Secondary alcohols Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Long chain fatty alcohol - Secondary alcohol - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Alcohol - Aliphatic acyclic compound
• Descrição: This compound belongs to the class of organic compounds known as long-chain fatty alcohols. These are fatty alcohols that have an aliphatic tail of 13 to 21 carbon atoms.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mecanismos de ação

Propriedades químicas e físicas

• Ponto de ebulição (°C): 135° C at 0.1 kPa
• Ponto de fusão (°C): 43-46 °C (lit.)
• Peso molecular: 242.440 g/mol
• XLogP3: 7.200
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 13
• Exact Mass: 242.261 Da
• Monoisotopic Mass: 242.261 Da
• Topological Polar Surface Area: 20.200 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 133.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

Not applicable. No validated bioassay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent in the Product Data. For synthetic or materials applications, see “Reaction Conditions” and “Synthetic Utility” for practical guidance.

Biological Roles

Context from biochemistry (literature/general knowledge; not specific to this item):

• Class: long-chain fatty alcohol. Such alcohols are components or precursors in wax esters, ether lipids, and lipid-derived signaling molecules in various organisms.
• Metabolism: In eukaryotes, fatty alcohols are typically oxidized by fatty alcohol dehydrogenases to the corresponding aldehydes and then to fatty acids, entering β-oxidation or esterification pathways. Chain length and branching/secondary structure influence enzyme affinity and rate.
• Membrane interactions: Hydrophobic C16 tails can intercalate into lipid bilayers; covalent derivatization (e.g., ester/ether linkages) is a common strategy to anchor functional groups or dyes to membranes in model systems.
• Surfactant/assembly behavior: When converted to esters, ethers, or quaternized derivatives, the C16 moiety acts as a hydrophobe driving micelle/vesicle formation; the secondary center may modulate packing and melting behavior compared with straight primary analogs.
• Biodegradation: Long-chain alcohols are generally biodegradable; oxidation proceeds via microbial alcohol/aldehyde dehydrogenases, though the secondary hydroxyl can slow initial oxidation relative to primary homologs.

No biological activity, potency, or clinical claims are made for this catalog item. Any biological discussion above is provided for research context only. For experimental use, confirm purity, isomerism (racemate vs enantioenriched), and absence of residual catalysts/impurities per CoA.

Buffer Applications

This compound is a hydrophobic secondary alcohol and is not used as a buffering agent. It lacks acid/base pairs in the physiological pH range and is practically insoluble in water, making it unsuitable for preparing aqueous buffer systems.

For experiments requiring aqueous manipulation, dissolve or disperse 2-hexadecanol in an appropriate organic cosolvent, emulsify with surfactants, or functionalize it to ionic/PEGylated derivatives; otherwise, see sections “Solvent Selection,” “Reaction & Applications,” and “Synthetic Utility” for more relevant guidance.

Green Alternatives

Greener choices revolve around renewable sourcing, safer solvents, and catalytic processes rather than the intrinsic hazard of this saturated alcohol (which already exhibits low volatility and low acute toxicity in typical handling).

• Renewable feedstocks: Long-chain alcohols can be bio-derived from plant oils, fatty acid reduction, or fermentation/hydrogenation routes. If supply chain sustainability is a priority, request documentation for bio-based content or ISCC certification for the specific lot (not specified for this item).
• Process alternatives (literature):
  • Enzymatic esterification using immobilized lipases (e.g., Novozym 435) in green solvents (2-MeTHF, CPME) or solvent-free melt conditions reduces energy and minimizes corrosive acids.
  • Oxidation to ketone via TEMPO/bleach or catalytic aerobic systems in MeCN/aqueous biphasic media avoids chromium waste; Swern/DMP remain effective but less green.
  • Substitution chemistry via sulfonates can be optimized in greener solvents (Cyrene, propylene carbonate) when solubility allows, or under solvent-free conditions with mechanochemistry.

Comparison (literature-based; qualitative):

• 1-Hexadecanol vs 2-Hexadecanol: Primary alcohol may offer milder oxidation/esterification and wider biocatalyst compatibility; however, secondary center of 2-hexadecanol provides access to ketones and stereochemical control (trade-off between reactivity and target structure).
• Solvents:
  • 2-MeTHF/CPME: improved EHS profile vs toluene/DCM; good for esterifications; may need drying controls.
  • Supercritical CO2: attractive for extraction/processing but requires specialized equipment.

Note: Selection should balance EHS gains with performance, procurement, and downstream specifications.

Pharmaceutical Uses

Item-specific regulatory/excipient status: Not specified for this item; refer to CoA/Spec Sheet.

General formulation context (literature/generic):

• Long-chain fatty alcohols (not specifically 2-hexadecanol) are used as emollients, viscosity modifiers, and consistency agents in ointments, creams, and solid dosage matrices. The secondary alcohol at C2 may impart a lower melting point and different crystallization behavior compared with the primary isomer (cetyl alcohol), potentially altering hardness and spreadability.
• Hydrophobic tail length (C16) supports formation of lamellar structures with fatty acids and surfactants, which can influence rheology and release characteristics in semi-solids.
• Derivatives (esters, ethers, carbonates, urethanes) of C16 alcohols are common lipophilic excipients and lubricant additives in solid dosage forms and topical vehicles. Selection is driven by melting behavior, peroxide value, odor/color, and regulatory monographs (e.g., Ph. Eur., USP) when applicable.

No therapeutic or clinical claims are made. If using in GMP or regulated contexts, verify compendial compliance, residual solvent levels, bioburden/endotoxin (if relevant), and supply chain documentation for the specific lot.

Physical Properties

Item-specific specifications are not provided in the Product Data.

Representative literature/computed values for 2-hexadecanol (for general guidance only; not specifications for this item):

• Physical state near ambient temperature: waxy solid or low-melting solid; may soften/liquefy slightly above room temperature depending on isomer ratio and history (literature).
• Melting point: typically reported ~26–30 °C (literature, racemic secondary C16 alcohols).
• Boiling point: commonly reported ~305–315 °C at 1 atm; distills more cleanly under reduced pressure (literature).
• Density: on the order of 0.82–0.84 g/mL in the molten state at ~30–40 °C (literature estimates for long-chain secondary alcohols).
• Refractive index (nD, liquid near melt): ~1.44–1.45 (literature, indicative for C16 alcohols).
• LogP (XLogP3-AA): ~7 (literature/computed for C16 alcohols).
• pKa (ROH/RO– in water): ~16–17 (literature, typical for aliphatic alcohols).
• Solubility: practically insoluble in water; soluble in nonpolar/aprotic organics (hexanes, toluene), chlorinated solvents, and moderately in lower alcohols upon warming (literature).

Item-specific values (appearance, exact mp/bp, density, UV cutoff, water, metals, etc.): Not specified for this item; refer to CoA/Spec Sheet.

Quality and Grades

• Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

Interpretation and implications (general guidance for long-chain alcohols):

• When a grade is not designated, users should verify assay, residual solvents, and key impurities (e.g., isomer content, unreacted olefins, peroxides typically low/absent for saturated alcohols) on the CoA before use in synthesis or formulation.
• For chromatographic or spectroscopic applications, low UV absorbance and low volatile/ionic impurities are desirable; an “HPLC grade” or “GC grade” designation, if present on a future lot, would indicate tighter control of such impurities.
• Stereochemistry: 2-hexadecanol contains a chiral center. If enantiopurity is critical (e.g., for chiral surfactant development), confirm whether the material is racemic or enantioenriched on the CoA.
• Water content and trace metals: Not specified for this item; refer to CoA/Spec Sheet. If moisture-sensitive downstream steps are planned (e.g., acid chlorides), consider drying (e.g., azeotrope, molecular sieves) and verifying Karl Fischer.
• Stabilizers/inhibitors: None specified. Long-chain saturated alcohols typically do not require stabilizers; confirm on CoA if any antioxidant or processing aid is present.
• Storage conditions: Room temperature (from Product Data). Ship: Normal (from Product Data).

Reaction and Applications

2-Hexadecanol is a versatile hydrophobic secondary alcohol used as a building block for surfactants, lubricants, and specialty materials. Representative applications (literature/generic):

• Esterification and transesterification: formation of long-chain secondary alkyl esters (e.g., 2-hexadecyl acetates, succinates) used as emollients and plasticizer components. Catalysts include mineral acids, p-TsOH, organocatalysts, or enzymatic (lipases) routes; water removal improves conversions.
• Oxidation to ketones: conversion to hexadecan-2-one using DMP, PCC, PDC, or Swern conditions. The resulting ketone is a useful intermediate for further elaboration (e.g., reductive amination to C16 secondary amines).
• Activation and substitution: formation of sulfonates (tosylate/mesylate) followed by SN2 displacement to install heteroatoms (Se, S, N) or form C–C bonds (via cyanide, malonate anions). Thionyl chloride or phosphorus halides can yield 2-chloro/bromohexadecane with inversion, enabling further functionalization.
• Ether formation: via Mitsunobu coupling (PPh3/DIAD or DEAD) with phenols/acids to form 2-hexadecyl ethers/esters with inversion at C2. Secondary centers may require optimization due to steric effects; choice of nucleophile pKa is critical.
• Dehydration: acid-catalyzed elimination to internal hexadecenes; useful for hydrophobic monomers or lubricant base stocks.
• Surface modification: grafting as a hydrophobic tail on silica, cellulose, or polymer backbones through ester/urethane linkages to tune wettability and barrier properties.
• Enzymatic routes: lipase-catalyzed acylations in nonaqueous media can proceed with high selectivity at modest temperatures, leveraging the long alkyl chain’s affinity for hydrophobic enzyme pockets.

Manufacturer applications: Not provided in Product Data; the above are literature-based examples.

Reaction Conditions

General literature guidance for common transformations of 2-hexadecanol (not item-specific; optimize per substrate and scale):

• Esterification (Fischer): carboxylic acid (1.2–2.0 equiv), catalytic p-TsOH (1–5 mol%), toluene or xylene, Dean–Stark, 90–130 °C, 4–16 h. Alternatively, Steglich esterification: acid (1.1 equiv), DCC (1.2 equiv), DMAP (5–10 mol%), DCM/THF, 0 °C to rt, 2–12 h.
• Oxidation to ketone:
  • Dess–Martin periodinane (1.3 equiv), DCM, 0 °C→rt, 1–3 h; typical high conversion with minimal overoxidation.
  • Swern (oxalyl chloride/DMSO, then Et3N), −78 °C→0 °C, DCM, 1–2 h.
  • Catalytic TEMPO/bleach (aqueous NaOCl, pH ~8.6, NaHCO3 buffer), biphasic DCM/MeCN–water, 0–25 °C; slower for secondary centers—optimize catalyst/phase transfer.
• Tosylation/mesylation: ROH (1.0 equiv), TsCl or MsCl (1.1–1.5 equiv), pyridine or DCM/Et3N, 0 °C→rt, 2–6 h; then SN2 with nucleophile in DMF/DMSO/MeCN, 50–100 °C.
• Halogenation: SOCl2 (1.5–3.0 equiv) with catalytic DMF in DCM or neat, 0 °C→reflux; or PBr3 (1.1–1.5 equiv), ether solvents, 0 °C→rt. Expect inversion at C2.
• Mitsunobu ether/ester formation: ROH (1.0 equiv), Nu–H (1.2–1.5 equiv), PPh3 (1.2 equiv), DIAD/DEAD (1.2 equiv), THF/THF–toluene, 0 °C→rt, 2–12 h; steric hindrance can reduce yields—use activated nucleophiles (pKa < 11) and warm if needed.
• Dehydration: catalytic H2SO4, p-TsOH, or POCl3/pyridine; 60–120 °C; mixture of internal alkenes—consider subsequent hydroboration–oxidation or epoxidation.

Solubility tips: warm to 35–50 °C to ensure homogeneity; use cosolvents (toluene/DCM) when employing polar media. Typical isolated yields in the 70–95% range are reported for optimized esterifications and oxidations.

Safety and Handling

GHS/SDS details for this specific lot are not provided in the Product Data.

• GHS classification, signal word, H-statements, pictograms: Not specified for this item; refer to the product SDS for authoritative information.
• General hazards (literature/generic for long-chain secondary alcohols): combustible solid/liquid above its melt; may cause skin and eye irritation; harmful if ingested in large quantities; slippery when molten. Low volatility reduces acute inhalation exposure under ambient conditions.
• Incompatibilities: strong oxidizing agents (risk of exothermic reaction); strong acids/bases can catalyze dehydration/esterification; avoid reactive acyl halides without controls.
• Handling advice:
  • Work with appropriate PPE: safety glasses, lab coat, and nitrile gloves; use heat-resistant gloves when handling molten material.
  • Minimize dust/aerosol formation when flaking or grinding a solidified mass.
  • If heating to liquefy, use controlled warming (30–60 °C) with secondary containment to prevent spills; do not overheat near ignition sources.
• First aid (general):
  • Skin: wash with soap and water; remove contaminated clothing.
  • Eyes: rinse cautiously with water for several minutes; seek medical attention if irritation persists.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
• Fire-fighting: use dry chemical, CO2, alcohol-resistant foam. Cool containers with water spray. Combustion may produce CO/CO2.
• Always consult the SDS for definitive hazard, exposure limits, and emergency measures.

Solvent Selection

This product is a hydrophobic reagent/building block rather than a general-purpose solvent. Selection here concerns dissolving or processing 2-hexadecanol effectively.

• Polarity and miscibility (literature): highly nonpolar with strong hydrophobic character; practically insoluble in water; freely soluble in nonpolar solvents (n-hexane, heptane, toluene), chlorinated solvents (DCM, chloroform), and moderately soluble in polar organics upon heating (THF, acetone, ethanol, isopropanol).
• Dielectric/solvent class (of common media): dissolves well in class II/III hydrocarbons and aromatics; requires warming for class II oxygenates.
• Practical guidance:
  • For esterifications or acylations: use toluene, xylene, or chlorinated solvents to keep the alcohol dissolved while removing water (Dean–Stark in aromatics) or operating under non-aqueous conditions.
  • For oxidations (e.g., Dess–Martin, Swern): DCM, CH2Cl2/Et2O, or THF often give good solubility; mild warming may be needed.
  • For substitution via sulfonates: perform tosylation/mesylation in pyridine, DCM, or acetonitrile; subsequent SN2 reactions benefit from polar aprotic media (DMF, DMSO) though solubility may require a cosolvent or temperature.
• Comparison (literature-based):
  • 1-Hexadecanol (cetyl alcohol) has similar solubility but a higher melting point; may require more heat to dissolve.
  • Shorter alcohols (C12–C14) dissolve more readily but change the hydrophobicity profile in formulations.
• Note: Always verify solvent compatibility with catalysts/reagents and desired workup; avoid strong oxidizers with molten alcohols.

Storage and Reconstitution

• Storage (from Product Data): Room temperature. Store tightly closed, in a dry place away from strong oxidizers. Normal shipping conditions are suitable.
• Physical handling: The compound may be a low-melting solid; if solidified, warm gently (30–50 °C) to liquefy before dispensing for accurate weighing or volumetric dosing. Avoid overheating and open flames.
• Inert atmosphere: Not strictly required for stability, but limiting prolonged exposure to air and light can minimize gradual oxidation or discoloration over long storage.
• Reconstitution/preparation of solutions:
  • Solubility: insoluble in water; soluble in hexanes, heptane, toluene, chloroform, DCM; moderately soluble in ethanol, isopropanol, THF upon warming (literature).
  • Stock solutions: prepare at 0.1–1.0 M in a compatible solvent (e.g., toluene, DCM, hexanes) depending on intended reaction; store in sealed amber glass if possible. For long-term stocks, refrigerate to slow oxidation and label with solvent and concentration.
• Freeze–thaw: Not applicable; no aqueous reconstitution required. If preparing dispersions/emulsions, use appropriate surfactants and record formulation conditions.
• Shelf life: Not specified for this item; refer to CoA/Spec Sheet. Inspect periodically for changes in color, odor, or peroxide formation (typically minimal for saturated alcohols). Research use only.

Structure and Identity

A saturated secondary fatty alcohol featuring a C16 linear chain with the hydroxyl at C2 (a chiral center), commonly handled as the racemate.

• SKU: H346541
• Product name: 2-Hexadecanol
• CAS: 14852-31-4
• PubChem CID: 85779 (literature)
• InChIKey: 93036 (from Product Data; truncated/not standard—refer to CoA/SDS for definitive identifier)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: C16H34O (literature)
• Molecular weight: 242.44 g/mol (literature)

Structural features (descriptive):

• Linear, unbranched alkyl chain of sixteen carbon atoms (hexadecyl) bearing a hydroxyl group on C2.
• One stereogenic center at C2; typical materials are racemic (RS)-2-hexadecanol unless otherwise specified.
• Functional group: secondary alcohol (–CHOH–), capable of oxidation to a ketone, esterification, ether formation after activation, and substitution via sulfonate/halide derivatives.
• 2D depiction in words: HO–CH(–C14H29)–CH3, i.e., the hydroxyl-bearing carbon is adjacent to the terminal methyl; the remainder is a straight n-tetradecyl segment.

Synthetic Utility

As a secondary C16 alcohol, 2-hexadecanol offers a balance of reactivity at C2 and a strongly hydrophobic tail, enabling diverse transformations:

• Oxidation: Clean conversion to hexadecan-2-one under Dess–Martin, PCC, or Swern conditions; ketone can undergo further C–C bond formation (Grignard/organolithium addition) to create tertiary alcohols retaining the C16 chain.
• Inversion/substitution: Formation of 2-chloro/bromohexadecane (SOCl2, PBr3) or sulfonate esters (MsCl/TsCl) allows SN2 reactions with O-, N-, S-, Se-, and C-nucleophiles, enabling ether, thioether, amine, azide, and nitrile derivatives.
• Mitsunobu couplings: Secondary alcohols can be coupled to phenols or carboxylic acids with inversion at C2, generating 2-hexadecyl aryl ethers or esters useful as hydrophobic anchors for materials and probes.
• Ester synthesis: Acid-catalyzed esterification or Steglich conditions (DCC/DMAP) furnish secondary esters with tailored melting points and viscosities (lubricant/emollient precursors).
• Dehydration/isomerization: Acid-catalyzed elimination to internal hexadecenes provides feedstocks for hydrophobes or further hydrofunctionalization (e.g., hydroboration–oxidation to migrate OH placement).
• Polymer and surface modification: Urethane formation (with diisocyanates) introduces C16 side chains into polyurethanes; silanol/acid chloride coupling to inorganic/organic surfaces imparts hydrophobic coatings.
• Chiral derivatives: If enantioenriched alcohol or chiral derivatization is used, the C2 stereocenter offers opportunities for stereochemical studies and chiral surfactant design.

These transformations leverage the stability of the saturated chain while exploiting the secondary center’s distinct reactivity relative to primary C16 alcohols.

Target Specificity

Not applicable. This product is a small-molecule fatty alcohol, not an antibody, enzyme, or ligand with defined biological target binding. No antigen/epitope, clone, isotype, or species reactivity is relevant.

Perguntas frequentes

How should this product be stored?

Store at room temperature.

What is the purity of this product?

This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How is this product shipped?

This product ships under standard ambient conditions. No temperature-controlled packaging is required.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 14852-31-4, the molecular formula is C16H34O, and the molecular weight is 242.44 g/mol. InChIKey FVDRFBGMOWJEOR-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.